US3900499A - (thio) phosphoric acid and (thio) phosphonic acid esters and amides - Google Patents
(thio) phosphoric acid and (thio) phosphonic acid esters and amides Download PDFInfo
- Publication number
- US3900499A US3900499A US342491A US34249173A US3900499A US 3900499 A US3900499 A US 3900499A US 342491 A US342491 A US 342491A US 34249173 A US34249173 A US 34249173A US 3900499 A US3900499 A US 3900499A
- Authority
- US
- United States
- Prior art keywords
- compound
- formula
- hydrogen
- alkyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001408 amides Chemical class 0.000 title description 3
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical class OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 title description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052717 sulfur Chemical group 0.000 claims abstract description 18
- 239000011593 sulfur Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical class C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract description 4
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 3
- 239000005645 nematicide Substances 0.000 abstract description 3
- 239000000642 acaricide Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- -1 O-alkyl Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KPNPDRFFWQBXGT-UHFFFAOYSA-N 1-dimethoxyphosphorylsulfanyl-2-ethylsulfanylethane;2-ethylsulfanylethoxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSCCOP(=S)(OC)OC.CCSCCSP(=O)(OC)OC KPNPDRFFWQBXGT-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- GGNLTHFTYNDYNK-UHFFFAOYSA-N Phenkapton Chemical compound CCOP(=S)(OCC)SCSC1=CC(Cl)=CC=C1Cl GGNLTHFTYNDYNK-UHFFFAOYSA-N 0.000 description 1
- 241000240376 Proteus anguinus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- SNZXMAHBUQXQSE-UHFFFAOYSA-N acetonitrile;benzene Chemical compound CC#N.C1=CC=CC=C1 SNZXMAHBUQXQSE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
- C07F9/097—Compounds containing the structure P(=O)-O-N
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1657—Compounds containing the structure P(=X)n-X-N (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/409—Compounds containing the structure P(=X)-X-acyl, P(=X) -X-heteroatom, P(=X)-X-CN (X = O, S, Se)
- C07F9/4096—Compounds containing the structure P(=X)-X-N (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4457—Compounds containing the structure C-P(=X)(X-acyl)-N, C-P(=X)(X-heteroatom)-N or C-P(=X)(X-CN)-N (X, Y = O, S)
Definitions
- R is O-alkyl, NH-alkyl or N-dialkyl
- R. is alkyl, O-alkyl or phenyl
- R and R are each hydrogen or alkyl
- R R R and R are each hydrogen, alkyl, halogen, alkoxy or alkylthio
- X is oxygen or sulfur, are useful as insecticides, acaricides and nematicides.
- the invention relates to novel (thio)phosphoric and (thio)phosphonic acid derivatives of the formula 5 amines of formula R H or R H, i.e. compounds in which R and R, represent O-alkyl, NH-alkyl, or N- dialkyl.
- R to R may have the following 5 meanings: 6-fluoro, 6-chloro, 6-bromo, 7-chloro, 7- 6 R 2 10 bromo, 5,8-dichloro-, 5,6,8-trichloro, 6-methyl, 2- 3 I methyl, 3-methyl, 6methoxy, 6-methylmercapto, 6- R R tert. butoxy, 6-ethoxy, 6-chloro-2-methyl, 6-chloro-3- 7 it methyl, 6chloro-5,8-dimethyl, the numbers indicating 8 the position of the substituents at the thiochromane nu- I cleus.
- Preferred are those compounds which are unsubin which stituted in the benzene moiety.
- R is O-alkyl, NHalkyl, or Ndialkyl
- the thiochromanone oximes of formula Ill used as R is alkyl, O-alkyl, or phenyl, the alkyl groups" of each starting material for carrying out the process of -the .in-
- R radical having one to 10 carbon atoms, vention as well as the salts"of"'th'es e""compounds are R, and R are each hydrogen or lower alkyl, partly described in literature (for example J. Ind. R ,R,;,R ,R,, each are hydrogen, lower alkyl, halogen, Chem. Soc. 43, pages 521 et seq. (1966). Those not yet lower alkoxy, or lower alkylthio, disclosed may be prepared in an analogous manner. and X is oxygen or sulfur.
- the starting compounds of formula II are known and Preferred alkyl groups are those having one to four readily accessible on an industrial scale by convencarbon atoms, preferably methyl and ethyl.
- the present invention also relates to a process for the The reaction is preferably carried out in a solvent manufacture of compounds of formula which comthat is inert under the reaction conditions, for example prises reacting (thio)ph sphoric or (thio)phosphonic CthCI'S, SUCh as thl, diiSOpI'Opyl ether, glycol id ester or id id h lid f f l dimethyl ether, tetrahydrofurane, dioxane; ketones and nitriles, such as acetone, methylethyl ketone, methylisopropyl ketone, methylbutyl ketone, benzonitrile, H propionitrile, acetonitrile; benzene and alkyl benzenes, H such as toluene or xylene; halobenzenes, for example chlorobenzene, dichlorobenzene; as well as
- Suitable acid-binding agents are especially alkali I11 metal alcoholates such as sodium or otassium meth l- R R y 14 ate or ethylate; sodium hydride, alkali metal carbonates R such as sodium carbonate and potassium carbonate, as
- tertiary bases for example triethyl amine or pyridine.
- ester halides or amide halides of formula 1 (R or R hal) obtained are then reacted with alcohols or Instead of the free thiochromanone oximes there may also be used the salts thereof, preferably the alkali metal and alkaline earth metal salts. In this case a basic agent need not be added.
- the thiochromanone oximes of formula [II can also be reacted with (thiono)phosphoric or (thiono)-
- the process of the invention can be carried out within a wide temperature range. In general, it is performed at room temperature or slightly or moderately elevated temperature, preferably in the range of from 20 to 100C. In most cases the reaction is exothermic and, therefore, it is often necessary, especially at the beginning of the reaction, to cool the reaction mixture Suitable dispersing agents are cellulose pitch (salts of lignin-sulfonic acids), salts of naphthalenesulfonic acid or, in certain cases, hydrated silicic acids or kieselguhr.
- suitable inorganc or organic from the outside.
- 5 salts for example sodium sulfate, ammonium sulfate, proved advantageous to continue stirring for a prosodium carbonate and sodium bicarbonate, sodium longed period of time (one to three hours) while heatthiosulfate, sodium stearate, or sodium acetate may be ing. used.
- the compounds of formula I are novel and represent WETTABLE POWDER a new class of phosphoric and phosphomc acld esters.
- the phosphoric and phosphonic acid derivatives of EMULSIFIABLE CONCENTRATE the invention may be formulated in admixture with solid or liquid inert carrier substances, adhesives, wet- 2 2 gf l kaftlve suinst'imcel, I: g of cyciohexanon; ans ting and dispersing agents, or grinding auxiliaries in the g 0 a y ary yg yco ct er f CO 0 are mlxe each other. 20 g of a 10% emulslfiable concentrate are form of wettable powders, emulsions, suspensions,
- EXAMPLE 50 Commercial phosphoric acid esters used for compar- Horse beans (Vicia faba) strongly infested with bean aphids (Doralisfabae) were sprayed to the drip-off with the aqueous dilution of an emulsion concentrate con- 50 taining as active ingredient 0.003% by weight of the compound of Example 1. The sprayed plants were placed in the greenhouse at 20C and the result was evaluated 24 hours after spraying. It was found that all aphids had been killed.
- EXAMPLE 51 Apple trees in pots strongly infested with a strain of 0 PE resistant fruit tree red spiders (Metatetranychus ulmi) were sprayed to the drip-off with the aqueous dilution of an emulsion concentrate containing as active ingredient 0.025% by weight of the compound of Example 3 and the plants were placed in the greenhouse at 20C. Examination under a microscope 8 days after the treatment showed that all movable stages of the mites had been killed.
- EXAMPLE 54 The bottoms and insides of five Petri dishes having a diameter of 9 cm were uniformly sprayed with 1 cc each of a 0.003% acetonic solution of the compound of Example 25. After evaporation of the acetone 10 house flies (musca domestica) were placed in each dish. Within 30 minutes all flies were in permanent dorsal position (moribund state) and died.
- R is O-alkyl, NH-alkyl, or Ndialkyl
- R is alkyl, O-alkyl, or phenyl
- R and R are each hydrogen or lower alkyl
- R R R R are each hydrogen, halogen, lower alkyl, lower alkoxy or lower alkylthio, the alkyl constituent of each of R, to R having 1 to 4 carbon atoms
- X is oxygen or sulfur.
- halogen is fluorine, chlorine or bromine
- the alkyl constituent of each of R to R is methyl or ethyl and at least one of R and R and at least three of R to R are hydrogen.
- substituents R to R are selected from the group consisting of 6- fluoro, 6-chloro, 6-bromo, 7-chloro, 7-brom0, 5,8- dichloro-, 5,6,8-trichl0ro, 6-methyl, 2-methyl, 3- methyl, 6-methoxy, 6-methylmercapto, 6-tert. butoxy, 6-ethoxy, 6-chloro-2-methyl, 6-chloro-3-methyl, 6- chloro-5,8dimethyl, said numbers indicating the position of the substituents at the thiochromane nucleus.
- R, and R are each methoxy, R is fluorine, R R R R and R, are each hydrogen and X is sulfur.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2214297A DE2214297A1 (de) | 1972-03-24 | 1972-03-24 | Neue (thio)phosphor- und (thio)phosphonsaeureester und -amide und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3900499A true US3900499A (en) | 1975-08-19 |
Family
ID=5839988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US342491A Expired - Lifetime US3900499A (en) | 1972-03-24 | 1973-03-19 | (thio) phosphoric acid and (thio) phosphonic acid esters and amides |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4479946A (en) * | 1980-06-27 | 1984-10-30 | Union Carbide Corporation | Phosphorus esters of amidoximes, and compositions for and methods of controlling insects using them |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204828A (en) * | 1978-08-01 | 1980-05-27 | Allied Chemical Corporation | Quench system for synthetic fibers using fog and flowing air |
| FI79535C (fi) * | 1982-05-06 | 1990-01-10 | Erba Farmitalia | Foerfarande foer framstaellning av dihydrobensopyrans och dihydrobensotiopyrans substituerade iminoderivat. |
| JPS61160417A (ja) * | 1985-01-08 | 1986-07-21 | Asahi Chem Ind Co Ltd | ポリヘキサメチレンアジパミド繊維の製造法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1164596A (en) * | 1967-04-05 | 1969-09-17 | Philips Nv | Oxime Derivatives |
-
1972
- 1972-03-24 DE DE2214297A patent/DE2214297A1/de active Pending
-
1973
- 1973-03-17 ES ES412792A patent/ES412792A1/es not_active Expired
- 1973-03-19 NL NL7303815A patent/NL7303815A/xx unknown
- 1973-03-19 ZA ZA731878A patent/ZA731878B/xx unknown
- 1973-03-19 US US342491A patent/US3900499A/en not_active Expired - Lifetime
- 1973-03-21 CH CH410173A patent/CH575716A5/xx not_active IP Right Cessation
- 1973-03-22 AT AT254573A patent/AT328792B/de not_active IP Right Cessation
- 1973-03-22 DD DD169655A patent/DD107852A5/xx unknown
- 1973-03-22 IT IT21995/73A patent/IT987039B/it active
- 1973-03-22 IL IL41849A patent/IL41849A/xx unknown
- 1973-03-23 JP JP48032805A patent/JPS496129A/ja active Pending
- 1973-03-23 GB GB1420473A patent/GB1391398A/en not_active Expired
- 1973-03-26 FR FR7310753A patent/FR2177981B1/fr not_active Expired
- 1973-03-26 BE BE129280A patent/BE797348A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1164596A (en) * | 1967-04-05 | 1969-09-17 | Philips Nv | Oxime Derivatives |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4479946A (en) * | 1980-06-27 | 1984-10-30 | Union Carbide Corporation | Phosphorus esters of amidoximes, and compositions for and methods of controlling insects using them |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5362973A (en) | 1974-09-26 |
| ATA254573A (de) | 1975-06-15 |
| BE797348A (fr) | 1973-09-26 |
| IL41849A (en) | 1975-07-28 |
| FR2177981B1 (US07902200-20110308-C00004.png) | 1976-09-10 |
| AT328792B (de) | 1976-04-12 |
| ES412792A1 (es) | 1976-09-01 |
| GB1391398A (en) | 1975-04-23 |
| JPS496129A (US07902200-20110308-C00004.png) | 1974-01-19 |
| ZA731878B (en) | 1973-12-19 |
| NL7303815A (US07902200-20110308-C00004.png) | 1973-09-26 |
| IT987039B (it) | 1975-02-20 |
| DE2214297A1 (de) | 1973-10-11 |
| CH575716A5 (US07902200-20110308-C00004.png) | 1976-05-31 |
| DD107852A5 (US07902200-20110308-C00004.png) | 1974-08-20 |
| IL41849A0 (en) | 1973-05-31 |
| FR2177981A1 (US07902200-20110308-C00004.png) | 1973-11-09 |
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